Over the next decade there will be an explosion of high quality kinematical data on hundreds of millions of stars in the Milky Way’s stellar halo. We are using cosmological hydrodynamical simulations to explore what we can learn about the detailed assembly history of the Milky Way from these data. We have analyzed orbits of halo stars and correlations between orbital properties and intrinsic stellar properties such as stellar ages and metallicities. I will discuss what halo orbits can tell us about halo assembly. I will also discuss predictions from simulations regarding the velocity anisotropy of the stellar halo and what recent observations of this quantity may (or may not) be telling us about the assembly of the Milky Way. Finally, in order to be able to use kinematical data on halo stars to infer the phase space distribution function of the stellar halo, we need to measure the potential of the dark matter halo. I will briefly discuss past work in this area and on going efforts to develop a new method to measure the shape of the Milky’s halo.